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Chapter 4 175
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69.
Mevacor has eight asymmetric centers, which are indicated by stars.
O
O
O
HO
*
*
*
*
*
*
*
*
O
70.
a.
Z
b.
E
c.
E
d.
Z
e.
E
f.
E
71.
a.
diastereomers (one asymmetric center has the same configuration in both compounds, and the other
has the opposite configuration in both compounds)
b.
enantiomers (they are mirror images)
c.
constitutional isomers
d.
diastereomers (the configuration of two asymmetric centers is the same, and the configuration of one
asymmetric center is different)
e.
diastereomers
f.
identical
g.
diastereomers
h.
indetical
72.
CH CH
2
>
CH(CH
3
)
2
>
CH
2
CH
2
CH
3
> CH
3
OH > NH
2
>
CH
2
OH > CH
2
NH
2
Cl > C( O)CH
3
> C N > CH CH
2
a.
b.
c.
73.
a.
H
H
I
I
F
F
b.
H
H
I
F
I
F
c.
H
H
F
I
I
F
74.
Only the compound on the far right is optically active, because it is the only one that has one or more
asymmetric centers.
75.
a.
Because there are two asymmetric centers, there are four stereoisomers.
b.
C C
H
HO
CH
3
H
NHCH
3
R
S